SU544656A1 - The method of obtaining unsubstituted imides of aromatic di- or tetracarboxylic acids - Google Patents
The method of obtaining unsubstituted imides of aromatic di- or tetracarboxylic acidsInfo
- Publication number
- SU544656A1 SU544656A1 SU2120474A SU2120474A SU544656A1 SU 544656 A1 SU544656 A1 SU 544656A1 SU 2120474 A SU2120474 A SU 2120474A SU 2120474 A SU2120474 A SU 2120474A SU 544656 A1 SU544656 A1 SU 544656A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- aromatic
- obtaining
- tetracarboxylic acids
- imides
- formamide
- Prior art date
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- Indole Compounds (AREA)
Description
1one
Изобретение относитс к органической технологии , конкретно к способу получени имидов карбоновых кислот.The invention relates to organic technology, specifically to a process for the preparation of carboxylic acid imides.
Имиды карбоновых кислот наход т широкое применение в качестве добавок к смазочным материалам, мономеров, пластификаторов, красителей, фармацевтических препаратов и т. д.Carboxylic acid imides are widely used as additives to lubricants, monomers, plasticizers, dyes, pharmaceuticals, etc.
Известен способ получени незамещенных ИМИДОВ кип чением ангидридов с 15-кратным избытком формамида в течение 1-6 час . Выход целевых продуктов достигает 52-88%.A known method for preparing unsubstituted IMIDES by boiling anhydrides with a 15-fold excess of formamide for 1-6 hours. The yield of the target products reaches 52-88%.
Недостатки способа св заны с необходимостью применени большого избытка дорогого и токсичного формамида, возможностью протекани побочных реакций, трудностью регенерации неустойчивого формамида и загр знением окружающей среды отходами производства .The disadvantages of the method are associated with the need to use a large excess of expensive and toxic formamide, the possibility of side reactions, the difficulty of regenerating unstable formamide and the pollution of the environment with production waste.
С целью сокращени расхода сырь реакцию ангидрида с формамидом, который берут с небольшим (0,2-0,5 моль) избытком, осуществл ют в органическом растворителе. Наиболее подход щими растворител ми вл ютс диметилформамид и диметилацетамид, предпочтительно диметилформамид.In order to reduce the consumption of the raw material, the reaction of the anhydride with formamide, which is taken with a slight (0.2-0.5 mol) excess, is carried out in an organic solvent. The most suitable solvents are dimethylformamide and dimethylacetamide, preferably dimethylformamide.
Оказалось, что в данном случае диалкиламиды не вступают во взаимодействие с ангидридами и не дают соответствующих примесей .It turned out that in this case dialkylamides do not interact with anhydrides and do not give the corresponding impurities.
Дл осуществлени целевого превращени исходные соединени кип т т в растворителе в течение 2-2,5 час. По охлаждении целевые ИМИДЫ выкристаллизовываютс с выходами 40-78%.To accomplish the desired conversion, the starting compounds are boiled in a solvent for 2-2.5 hours. Upon cooling, the desired IMIDS crystallize out in yields of 40-78%.
Следующие примеры иллюстрируют, но не ограничивают предлагаемый способ.The following examples illustrate, but do not limit the proposed method.
Пример 1. Диимид пиромеллитовой кислоты .Example 1. Pyromellitic acid diimide.
Л. Смесь 1 г диангидрида пиромелитовой кислоты, 0,516 г (0,5 мол рный избыток) формамида и 5 мл диметилформамида кип т т с обратным холодильником в течении 100 мин. По охлаждении до комнатной температуры образуетс зеленоватый осадок. Его отфильтровывают .L. A mixture of 1 g of pyromelytic dianhydride, 0.516 g (0.5 molar excess) of formamide and 5 ml of dimethylformamide is heated under reflux for 100 minutes. Upon cooling to room temperature, a greenish precipitate is formed. It is filtered out.
Выход целевого продукта составл ет 0,85 г; т. пл. 450-455°С (разлолсенне).The yield of the target product is 0.85 g; m.p. 450-455 ° C (rasolsenne).
Найдено, %: С 55,4; Н 1,7; N 12,5.Found,%: C 55.4; H 1.7; N 12.5.
Вычислено, %: С 55,6; Н 1,9; N 13,0.Calculated,%: C 55.6; H 1.9; N 13.0.
ИК-сиектр: 1710, 1730, 1760, 1790 см-.IR spectrum: 1710, 1730, 1760, 1790 cm-.
Из маточного раствора после упаривани растворител получают дополнительно 0,07 г имида пиромеллитовой кислоты. Общий выход 93%.An additional 0.07 g of pyromellitic acid imide is obtained from the mother liquor after evaporation of the solvent. Total yield 93%.
Б. Вместо диметилформамида примен ют диметилацетамид. Выход имида составл ет 78,9%.B. Dimethylacetamide is used instead of dimethylformamide. The imide yield is 78.9%.
Пример 2. Имид тетрахлорфталевой кислоты .Example 2. Imid tetrachlorophthalic acid.
Смесь 0,5 г ангидрида тетрахлорфталевой кислоты, 0,173 г (0,2 мол рный избыток) формамида и 2,5 мл диметилформамида кин т т 2,5 час. После обработки (по примеру 1) получают 0,2 г (40,2%) целевого продукта с т. пл. 338-339°С.A mixture of 0.5 g of tetrachlorophthalic anhydride, 0.173 g (0.2 molar excess) of formamide, and 2.5 ml of dimethylformamide is used for 2.5 hours. After treatment (according to Example 1), 0.2 g (40.2%) of the desired product is obtained with a mp. 338-339 ° C.
Найдено, %: С 33,69; Н 0,41; N 4,85; С1 49,9.Found,%: C 33.69; H 0.41; N 4.85; C1 49.9.
Вычислено, %: С 33,72; Н 0,35; N 4,92; С1 49,78.Calculated,%: C 33.72; H 0.35; N 4.92; C1 49.78.
ИК-спектр: 1700, 1715, 1760, 1770 см-.IR spectrum: 1700, 1715, 1760, 1770 cm-.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU2120474A SU544656A1 (en) | 1975-04-07 | 1975-04-07 | The method of obtaining unsubstituted imides of aromatic di- or tetracarboxylic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU2120474A SU544656A1 (en) | 1975-04-07 | 1975-04-07 | The method of obtaining unsubstituted imides of aromatic di- or tetracarboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU544656A1 true SU544656A1 (en) | 1977-01-30 |
Family
ID=20614971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2120474A SU544656A1 (en) | 1975-04-07 | 1975-04-07 | The method of obtaining unsubstituted imides of aromatic di- or tetracarboxylic acids |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU544656A1 (en) |
-
1975
- 1975-04-07 SU SU2120474A patent/SU544656A1/en active
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